1,2,3,4-Tetrahydroisoquinoline → Benzamide, 3,4-dimethoxy-N-(1,2,3,4-tetrahydro-2-methylisoquinolin-5-yl)-

HRID 2397932Notes

Reaction equation

HRID 2397932 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7]2.C(=O)(O)[O-].[K+].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:23](Cl)=[O:24].C1C2C(=CC=CC=2)CCN1>C1C=CC=CC=1>[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:23]([NH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([CH3:12])[CH2:7]2)=[O:24]

Participants

6

Reactant 4

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 77070Veratroyl chlorideHCID 516893Potassium BicarbonateHCID 141712692-Methyl-1,2,3,4-tetrahydroisoquinolin-5-amine

Product 1

HCID 216587Benzamide, 3,4-dimethoxy-N-(1,2,3,4-tetrahydro-2-methylisoquinolin-5-yl)-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5-Amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (12.9 g) prepared as in Example 4 was dissolved in dry benzene (100 ml) and 0.5 g of dry potassium bicarbonate was added. A 0.1 mole excess of 3,4-dimethoxybenzoyl chloride was dissolved in dry benzene (100 ml) and this solution was added to the solution of the tetrahydroisoquinoline. A precipitate formed immediately and the mixture was refluxed for 1 hour. The precipitate was collected by filtration and washed with 10% sodium carbonate solution followed by water. The washings were discarded and the remaining residue was recrystallized from ethanol to yield 12.0 g of the desired product as a white powder, m.p. 160°-161.5° C.

Workup

  1. customA precipitate formed immediately
  2. temperaturethe mixture was refluxed for 1 hour
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with 10% sodium carbonate solution
  5. customthe remaining residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-ac106836cbc64aaabc340698ff2349d6
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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